25 Can’t-Miss Things to Do Along the Chesapeake Bay
Play, sight-see, eat, socialize, collect and explore along Maryland’s famous estuary. Use these 25 ideas for things to see and do along the Chesapeake to get you going.
Things to See and Do in Southern Maryland
In Southern Maryland, history and culture mingle on the shores of the Chesapeake Bay.
Things to See and Do in Central Maryland
From Annapolis—Maryland’s capital city and the Sailing Capital of the World—to the eclectic fun of Baltimore, to the Piedmont forests and the shores of the Chesapeake Bay, the Central Region offers thriving cultural destinations, history, music and more.
Things to See and Do on the Eastern Shore
Maryland’s Eastern Shore is home to spectacular sunsets, world-class seafood and produce, nature, history and so much more.
Nifty off 50
U.S. Route 50 is the major east-west route of the U.S. Highway system and it starts and cuts right through Maryland. Be sure to see the unique places and people along this iconic road.
Art of the Chesapeake
Discover the best galleries and arts events and learn about the unique art of Maryland’s Chesapeake Bay.
National and State Parks
Get in touch with the lives of great Americans like Harriet Tubman, Clara Barton and Thomas Stone. See historic places like Fort McHenry and the Chesapeake and Ohio Canal where the very course of history was changed. Lose yourself in one of a kind landscapes at public parks like Assateague, Sandy Point and Blackwater.
Maryland’s Maritime Museums
Maryland's maritime museums offer so much to explore. Touch and experience the Chesapeake Bay's marine creatures up-close and discover how they live. Explore a boat-building workshop and get an insider's look at the life of a waterman. She how people depend upon a healthy bay.
Tour Maryland’s Lighthouses
Tour these beautiful historic beacons and enjoy the surrounding nature and vistas of the Chesapeake Bay.
Touring the Islands of Maryland
Maryland is home to hundreds of islands just waiting to be explored.
Some are uninhabited or strictly nature preserves, while others are home to shops,
restaurants and museums.
Boating and Water Sports
Maryland's waterways are a defining feature of the Old Line State, and no visit is complete without leaving the land behind, even for just a little while.
Maryland Crab & Oyster Trail
Savor the fruits of the Chesapeake Bay on the Maryland Crab & Oyster Trail.
Wine Trails Along the Great Chesapeake Bay Loop
Maryland’s distinct microclimates provide diversity and flavor to our wines. Three of the Maryland’s eight wine trails are part of the Great Chesapeake Bay Loop.
Chesapeake Wine Trail, this trail is the perfect excuse to explore the treasures of the Eastern Shore
Legacy Wine Trail, Southern Maryland's agricultural heritage meets the new legacy of fine wine.
Patuxent Wine Trail, Southern Maryland capitalizes on its Old-World growing traditions to bring an exciting new vision to classic wine profiles.
Waterside Events and Festivals
Whether you want to make a splash or just watch, waterside events abound in Maryland.
More About the Great Chesapeake Bay Loop
To help you plan your Chesapeake Bay adventure, here’s some suggestions to get the most memories per mile: